Quadratic hyperpolarizability enhancement of para-substituted pyridines upon coordination to organometallic moieties: The ambivalent donor or acceptor role of the metal

Organometallics

Volumn 19, Issue 9, 2000, Pages 1775-1788

  Roberto, Dominique ^a   Ugo, Renato ^a   Bruni, Silvia ^a   Cariati, Elena ^a   Cariati, Franco ^a   Fantucci, PierCarlo ^a   Invernizzi, Ivana ^a   Quici, Silvio ^b   Ledoux, Isabelle ^c   Zyss, Joseph ^c  

^a UNIVERSITY OF MILAN   (Italy)

^b CNR   (Italy)

^c LABORATOIRE DE PHOTONIQUE QUANTIQUE ET MOLÉCULAIRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001634843     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990865p     Document Type: Article

References (79)

1. (a) Nalwa, H. S. Appl. Organomet. Chem. 1991, 5, 349.
2. (b) Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21.
3. Zyss, J. Molecular Nonlinear Optics; Academic Press: New York, 1994.
4. Optoelectronic Properties of Inorganic Compounds; Roundhill, D. M., Fackler, J. P. Jr., Eds.; Plenum Press: New York, 1999.
5. (a) Zyss, J. J. Non-Cryst. Solids 1982, 47, 211.
6. (b) Williams, D. J. Angew. Chem., Int. Ed. Engl. 1984, 23, 690.
7. (c) Meredith, G. R. Mater. Res. Bull. 1988, August, 24.
8. (d) Tripathy, S.; Cavicchi, E.; Kumar, J.; Kumar, R. S. Chemtech 1989, 19, 620.
9. (e) Marder, S. R.; Perry, J. W.; Yakymyshyn, C. P. Chem. Mater. 1994, 6, 1137.
10. (f) Optical Nonlinearities in Chemistry. Chem. Rev. 1994, 94, 4, Issue No. 1 (Introduction by Burland, D. M.).
11. (a) Cheng, L. T.; Tam, W.; Stevenson, S. H.; Meredith, G. R.; Rikken, G.; Marder, S. R. J. Phys. Chem. 1991, 95, 10631.
12. (b) Cheng, L. T.; Tam, W.; Marder, S. R.; Stiegman, A. E.; Rikken, G.; Spangler, C. W. J. Phys. Chem. 1991, 95, 10643.
13. (a) Oudar, J. L. J. Chem. Phys. 1977, 67, 446.
14. (b) Oudar, J. L.; Chemla, D. S. J. Chem. Phys. 1977, 66, 2664.
15. (c) Oudar, J. L.; Le Person, H. Opt. Commun. 1975, 15, 258.
16. (a) Cheng, L. T.; Tam, W.; Meredith, G. R.; Marder, S. R. Mol. Cryst. Liq. Cryst. 1990, 189, 137.
17. (b) Cheng, L. T.; Tam, W.; Eaton, D. F. Organometallics 1990, 9, 2856.
18. Kanis, D. R.; Lacroix, P. G.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10089.
19. (a) Bruce, D. W.; Thornton, A. Mol. Cryst. Liq. Cryst. 1993, 231, 253.
20. (b) Briel, O.; Sunkel, K.; Krossing, I.; Noth, H.; Schmalzlin, E.; Meerholz, K.; Brauchle, C.; Beck; W. Eur. J. Inorg. Chem. 1999, 483.
21. -1) are quite different from those measured by us under similar conditions (Table 3).
22. (a) Bourgault, M.; Mountassir, C.; Le Bozec, H.; Ledoux, I.; Pucetti, G.; Zyss, J. J. Chem. Soc., Chem. Commun. 1993, 1623.
23. (b) Bourgault, M.; Baum, K.; Le Bozec, H.; Pucetti, G.; Ledoux, I.; Zyss, J. New. J. Chem. 1998, 517.
24. (c) Peng, Z.; Yu, L. J. Am. Chem. Soc. 1996, 118, 3777.
25. (a) Di Bella, S.; Fragalà, I.; Ledoux, I.; Diaz-Garcia, M. A.; Lacroix, P. G.; Marks, T. J. Chem. Mater. 1994, 6, 881.
26. (b) Di Bella, S.; Fragalà, I.; Ledoux, I.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 9481.
27. (c) Lacroix, P. G.; Di Bella, S.; Ledoux, I. Chem. Mater. 1996, 8, 541.
28. (a) Calabrese, J. C.; Tam, W. Chem. Phys. Lett., 1987, 133, 244.
29. (b) Cummings, S. D.; Cheng, L. T.; Eisenberg, R. Chem. Mater. 1997, 9, 440.
30. De la Torre, G.; Vasquez, P.; Agullo-Lopez, F.; Torres, T. J. Mater. Chem. 1998, 8, 1671, and references therein.
31. (a) Le Cours, S. M.; Guan, H. W.; Di Magno, S. G.; Wang, C. H.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1497.
32. (b) Suslick, K. S.; Chen, C. T.; Meredith, G. R.; Cheng, L. T. J. Am. Chem. Soc. 1992, 114, 6928.
33. (c) Yeung, M.; Ng, A. C. H.; Drew, M. G. B.; Vorpagel, E.; Breitung, E. M.; McMahon, R. J.; Ng, D. K. P. J. Org. Chem. 1998, 63, 7143.
34. (a) Levine, B. F.; Bethea, C. G. Appl. Phys. Lett. 1974, 24, 445.
35. (b) Singer, K. D.; Garito, A. F. J. Chem. Phys. 1981, 75, 3572.
36. (c) Ledoux, I.; Zyss, J. Chem. Phys. 1982, 73, 203.
37. Roberto, D.; Cariati, E.; Psaro, R.; Ugo, R. Organometallics 1994, 13, 4227.
38. Herde, J. L.; Lambert, J. C.; Senoff, C. V. Inorg. Synth. 1974, 15, 18.
39. (a) Lawson, D. N.; Wilkinson, G. J. Chem. Soc. 1965, 1900.
40. (b) Roberto, D.; Psaro, R.; Ugo, R. Organometallics 1993, 12, 2292.
41. Giordano, G.; Crabtree, R. H. Inorg. Synth. 1979, 19, 218.
42. (a) Psaro, R.; Dossi, C. Inorg. Chim. Acta 1983, 77, L255.
43. (b) Hermann, W. A.; Herdtweck, E.; Schofer, A. Chem. Ber. 1988, 121, 1907.
44. (a) Guggenheim, E. A. Trans. Faraday Soc. 1949, 45, 203.
45. (b) Smith, W. Electric Dipole Moments; Butterworth Scientific Publications: London, 1965.
46. (c) Thompson, B. J. Chem. Educ. 1996, 43, 66.
47. (a) Leffler, J. E.; Grunwald, E. Rates and Equilibria of Organic Reaction; Wiley: New York, 1963.
48. (b) Jaffè, H. H. Chem. Rev. 1953, 53, 19.
49. (a) Wrighton, M. S.; Abrahamson, H. B.; Morse, D. L. J. Am. Chem. Soc. 1976, 98, 4105.
50. (b) Geoffroy, G. L.; Wrighton, M. S. Organometallic Photochemistry; Academic Press: New York, 1979.
51. (a) Chatt, J.; Williams, A. A. J. Chem. Soc. 1951, 3061.
52. (b) Chatt, J.; Hart, F. A. J. Chem. Soc. 1960, 1378.
53. Steigman, A. E.; Miskowski, V. M.; Perry, K. J.; Coulter, D. R. J. Am. Chem. Soc. 1987, 109, 5884.
54. Bruni, S.; Cariati, E.; Cariati, F.; Porta, F.; Quici, S.; Roberto, D. Manuscript in preparation.
55. Bruni, S.; Cariati, E.; Cariati, F.; Porta, F.; Quici, S.; Roberto, D. Manuscript in preparation.
56. Kurtz, S. K.; Perry, T. T. J. Appl. Phys. 1968, 39, 3798.
57. (a) Willetts, A.; Rice, J. E.; Burland, D. M.; Shelton, D. P. J. Chem. Phys. 1992, 97, 7590.
58. (b) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195.
59. (c) Shelton, D. P.; Rice, J. E. Chem. Rev. 1994, 94, 3.
60. Orr, B. J.; Ward, J. F. Mol. Phys. 1971, 20, 513.
61. (a) Ridley J. E.; Zerner, M. C. Theor. Chim. Acta (Berlin) 1973, 32, 111
62. (b) Ridley J. E.; Zemer, M. C. Theor. Chim. Acta (Berlin) 1976, 42, 223
63. (c) Bacon, A. D.; Zerner, M. C. Theor. Chim. Acta (Berlin) 1979, 53, 21.
64. (d) Anderson, W. P.; Edwards, W. D.; Zerner, M. C. Inorg. Chem. 1986, 25, 2728.
65. (e) Kotzian, M.; Rösch, N.; Schröder, H.; Zerner, M. C. J. Am. Chem. Soc. 1989, 111, 7687.
66. (a) Sekino, H.; Bartlett, R. J. Chem. Phys. 1986, 85, 976.
67. (b) Sekino, H.; Bartlett, R. J. Chem. Phys. 1991, 94, 3665.
68. Karna, S. P.; Dupuis, M. J. Comput. Chem. 1991, 12, 487.
69. Ågren H.; Vahtras, O.; Koch, H.; Jørgensen, P.; Helgaker, T. J. Chem. Phys. 1993, 98, 6417.
70. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4899.
71. Kanis, D. R.; Marks, T. J.; Ratner, M. A. Int. J. Quantum Chem. 1992, 43, 61.
72. Singer, K. D.; Sohn, E.; King, L. A.; Gordon, H. M.; Katz, H. E.; Dirk, P. W. J. Opt. Soc. Am. B 1989, 6, 1339.
73. Gerrat, J.; Mills, I. M. J. Chem. Phys. 1968, 49, 1719.
74. MOPAC Manual (6th ed.), a program product of Stewart, J. J. P., and Seiler, F. J. Research Laboratory-United States Air Force Academy, 1990.
75. Dupuis, M.; Farazdel, A.; Karna, S. P.; Maluendes, S. A. HONDO-8 in Modern Techniques in Computational Chemistry; MOTECC-90; Clementi, E., Ed.; ESCOM: Leiden, 1990.
76. Ditchfield, R.; Hehere, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
77. Pentimelli, L. Gazz. Chim. Ital. 1961, XCI, 991.
78. 13C nuclei, confirming our assignments.
79. McClellan, A. L. Tables of experimental dipole moments; W. H. Freeman and Co.: San Francisco, 1963.